Exp181

Edit 0 101 …

Objective

To synthesize 66 Ugi adducts using Ugi 4CR following Explan005 .The target compound were ranked 55 -124 (except 58) in the DEXP014-V2B file from D-EXP014 . The purpose of this experiment is to synthesize an anti-malarial compound based on the inhibition of falcipain-2, as described in this summary post .

Procedure

To sixty nine vials, labeled 181# (55-124 except 58) and charged with methanol, four reactants [aldehyde, amine, acid and isocyanide] (0.5mmol each) were added to each in that order. After each addition, the resulting solution was vortexed for 30seconds (or more) . The vials were capped tight and left at room temperature. The vials which formed solid precipitates or crystals were decanted and the solid was washed with methanol (3x 500uL) and dried under vacuum to obtain corresponding Ugi products.

Exp-Lib Rank
 Aldehyde
 Amine
 Acid
 Isocyanide
 Ppt (Y/N) & Yield
181-55
 Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
 5-Methylfurfurylamine
(0.5mmol-55.7uL)
 2,6-dihydroxybenzoic aicd
(0.5mmol-77.0mg)
 n-butylisocyanide
(0.5mmol-53uL)
 N
181-56
 Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
 Furfurylamine
(0.5mmol-44.2uL)
 2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
 n-butylisocyanide
(0.5mmol-53uL)
 Reactants
Insoluble
181-57
 Salicylaldehyde
(0.5mmol-53.3uL)
 Methylamine
(0.5mmol-250uL)
 Phenylpropynoic acid
(0.5mmol-73.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-59
 o-tolualdehyde
(0.5mmol-57.8uL)
 Methylamine
(0.5mmol-250uL)
 4-hydroxybenzoic acid
(0.5mmol-69mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-60
 Salicylaldehyde
(0.5mmol-53.3uL)
 Furfurylamine
(0.5mmol-44.2uL)
 Phenylpropynoic acid
(0.5mmol-73.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-61
 2,4,6-trimethylbenzaldehyde -(spoilt)
(0.5mmol-73.8uL)
 3-Chloroaniline
(0.5mmol-53uL)
 alpha-hydroxyphenylacetic acid
(0.5mmol-76mg)
 TOSMIC
(0.5mmol-97.6mg)
 N/A
181-62
 3,5-dimethoxybenzaldehyde
(0.5mmol-83.1mg)
 Methylamine
(0.5mmol-250uL)
 4-hydroxybenzoic acid
(0.5mmol-69mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-63
 Salicylaldehyde
(0.5mmol-53.3uL)
 Propylamine
(0.5mmol-41.1uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-64
 3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
 1-hexylamine
(0.5mmol-66ul)
 3-Methyl-2-butenoic acid
(0.5mmol-50.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-65
 3,5-dimethoxybenzaldehyde
(0.5mmol-83.1mg)
 Benzylamine
(0.5mmol-54.6uL)
 Quinic Acid
(0.5mmol-96.1mg)
 t-butylisocyanide
(0.5mmol-57.5uL)
 N
181-66
 3-hydroxybenzaldehyde
(0.5mmol-61.0mg)
 Methylamine
(0.5mmol-250uL)
 2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-67
 4-hydroxybenzaldehyde
(0.5mmol-61mg)
 Furfurylamine
(0.5mmol-44.2uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-68
 o-vanillin
(0.5mmol-76.0mg)
 Methylamine
(0.5mmol-250uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-69
 2-naphthaldehyde
(0.5mmol- 78.1mg)
 Aniline
(0.5mmol-45.5uL)
 2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
 TOSMIC
(0.5mmol-97.6mg)
 Reactants
Insoluble
181-70
 o-tolualdehyde
(0.5mmol-57.8uL)
 3-Chloroaniline
(0.5mmol-53uL)
 1-Pyrenebutyric acid
(0.5mmol-144.1mg)
 n-butylisocyanide
(0.5mmol-53uL)
 Reactants
Insoluble
181-71
 Benzaldehyde
(0.5mmol-50.8uL)
 Benzylamine
(0.5mmol-54.6uL)
 alpha-hydroxyphenylacetic acid
(0.5mmol-76mg)
 TOSMIC
(0.5mmol-97.6mg)
 Y No Ugi product
181-72
 4-(trifluoromethyl)benzaldehyde
(0.5mmol-68.3uL)
 Methylamine
(0.5mmol-250uL)
 2,6-dihydroxybenzoic aicd.H2O
(0.5mmol-77.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-73
 Benzaldehdye
(0.5mmol-50.8uL)
 Methylamine
(0.5mmol-250uL)
 Boc-Trp-OH
(0.5mmol-152.1mg)
 t-butylisocyanide
(0.5mmol-57.5uL)
 N
181-74
 3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
 Aniline
(0.5mmol-45.5uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 t-butylisocyanide
(0.5mmol-57.5uL)
 N
181-75
 Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
 Furfurylamine
(0.5mmol-44.2uL)
 alpha-hydroxyphenylacetic acid
(0.5mmol-76mg)
 n-butylisocyanide
(0.5mmol-53uL)
 N
181-76
 3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
 Propylamine
(0.5mmol-41.1uL)
 diphenylaceitc acid
(0.5mmol-106.1mg)
 n-butylisocyanide
(0.5mmol-53uL)
 N
181-77
 3-methoxybenzaldehyde
(0.5mmol-61uL)
 5-Methylfurfurylamine
(0.5mmol-55.7uL)
 2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
 n-butylisocyanide
(0.5mmol-53uL)
 Reactants
Insoluble
181-78
 Salicylaldehyde
(0.5mmol-53.3uL)
 1-hexylamine
(0.5mmol-66ul)
 1-Pyrenebutyric acid
(0.5mmol-144.1mg)
 t-butylisocyanide
(0.5mmol-57.5uL)
 Reactants
Insoluble
181-79
 Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
 Furfurylamine
(0.5mmol-44.2uL)
 2,4,6-trihydroxybenzoic acid
(0.5mmol-94mg)
 t-butylisocyanide
(0.5mmol-57.5uL)
 Reactants
Insoluble
181-80
 3-methoxybenzaldehyde
(0.5mmol-61uL)
 Aniline
(0.5mmol-45.5uL)
 2,4,6-trihydroxybenzoic acid
(0.5mmol-94mg)
 TOSMIC
(0.5mmol-97.6mg)
 Y
181-81
 2-naphthaldehyde
(0.5mmol- 78.1mg)
 2-Chloroaniline
(0.5mmol-52.6uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 t-butylisocyanide
(0.5mmol-57.5uL)
 Reactants
Insoluble
181-82
 3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
 Furfurylamine
(0.5mmol-44.2uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-83
 Benzaldehye
(0.5mmol-50.8uL)
 Aniline
(0.5mmol-45.5uL)
 1-Pyrenebutyric acid
(0.5mmol-144.1mg)
 n-butylisocyanide
(0.5mmol-53uL)
 Reactants
Insoluble
181-84
 3-methoxybenzaldehyde
(0.5mmol-61uL)
 Benzylamine
(0.5mmol-54.6uL)
 alpha-hydroxyphenylacetic acid
(0.5mmol-76mg)
 n-butylisocyanide
(0.5mmol-53uL)
 N
181-85
 Salicylaldehyde
(0.5mmol-53.3uL)
 3-Chloroaniline
(0.5mmol-53uL)
 2,5-dimethoxyphenylacetic acid
(0.5mmol-98.1)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-86
 3-hydroxybenzaldehyde
(0.5mmol-61.0mg)
 Methylamine
(0.5mmol-250uL)
 4-hydroxybenzoic acid
(0.5mmol-69mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-87
 2,4-dimethylbenzaldehyde
(0.5mmol-69.7uL)
 Methylamine
(0.5mmol-250uL)
 1-Pyrenebutyric acid
(0.5mmol-144.1mg)
 t-butylisocyanide
(0.5mmol-57.5uL)
 Reactants
Insoluble
181-88
 3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
 5-Methylfurfurylamine
(0.5mmol-55.7uL)
 diphenylaceitc acid
(0.5mmol-106.1mg)
 n-butylisocyanide
(0.5mmol-53uL)
 N
181-89
 Salicylaldehyde
(0.5mmol-53.3uL)
 3-Chloroaniline
(0.5mmol-53uL)
 hexanoic acid
(0.5mmol-62.6uL)
 TOSMIC
(0.5mmol-97.6mg)
 Reactants
Insoluble
181-90
 3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
 Methylamine
(0.5mmol-250uL)
 4-Nitrobenzoic acid
(0.5mmol-83.5mg)
 TOSMIC
(0.5mmol-97.6mg)
 Reactants
Insoluble
181-91
 2-chloro-6-methylbenzaldehyde-(unavailable)
(05.mmol-77.3mg)
 Methylamine
(0.5mmol-250uL)
 Boc-Trp-OH
(0.5mmol-152.1mg)
 n-butylisocyanide
(0.5mmol-53uL)
 N/A
181-92
 3-methoxybenzaldehyde
(0.5mmol-61uL)
 2-Chloroaniline
(0.5mmol-52.6uL)
 Decanoic acid
(0.5mmol-96.5uL)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-93
 Salicylaldehyde
(0.5mmol-53.3uL)
 Aniline
(0.5mmol-45.5uL)
 hexanoic acid
(0.5mmol-62.6uL)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-94
 3,5-dimethoxybenzaldehyde
(0.5mmol-83.1mg)
 Furfurylamine
(0.5mmol-44.2uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-95
 2-chloro-6-methylbenzaldehyde-(unavailable)
(05.mmol-77.3mg)
 3-Chloroaniline
(0.5mmol-53uL)
 alpha-hydroxyphenylacetic acid
(0.5mmol-76mg)
 TOSMIC
(0.5mmol-97.6mg)
 N/A
181-96
 3-methoxybenzaldehyde
(0.5mmol-61uL)
 Methylamine
(0.5mmol-250uL)
 4-hydroxybenzoic acid
(0.5mmol-69mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-97
 Salicylaldehyde
(0.5mmol-53.3uL)
 Furfurylamine
(0.5mmol-44.2uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-98
 4-hydroxybenzaldehyde
(0.5mmol-61mg)
 Methylamine
(0.5mmol-250uL)
 2,3-dihydroxybenzoic acid.
(0.5mmol-77.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-99
 4-methoxybenzaldehyde
(0.5mmol-60.8uL)
 2-Chloroaniline
(0.5mmol-52.6uL)
 4-hydroxybenzoic acid
(0.5mmol-69mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-100
 4-chlorobenzaldehyde
(0.5mmol-70.3mg)
 Methylamine
(0.5mmol-250uL)
 Quinic Acid
(0.5mmol-96.1mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-101
 4,7-dimethoxy-1-naphthaldehyde
(0.5mmol-108.1mg)
 Methylamine
(0.5mmol-250uL)
 2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
 TOSMIC
(0.5mmol-97.6mg)
 Reactants
Insoluble
181-102
 3-hydroxybenzaldehyde
(0.5mmol-61.0mg)
 5-Methylfurfurylamine
(0.5mmol-55.7uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-103
 Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
 Methylamine
(0.5mmol-250uL)
 alpha-hydroxyphenylacetic acid
(0.5mmol-76mg)
 n-butylisocyanide
(0.5mmol-53uL)
 N
181-104
 4-(Dimethylamino)benzaldehyde
(0.5mmol-74.6mg)
 Methylamine
(0.5mmol-250uL)
 Quinic Acid
(0.5mmol-96.1mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-105
 3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
 t-butylamine
(05mmol-52.5uL)
 4-chlorophenylacetic acid
(0.5mmol-85.3mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-106
 2-naphthaldehyde
(0.5mmol- 78.1mg)
 Methylamine
(0.5mmol-250uL)
 4-hydroxybenzoic acid
(0.5mmol-69mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-107
 Salicylaldehyde
(0.5mmol-53.3uL)
 Aniline
(0.5mmol-45.5uL)
 Phenylpropynoic acid
(0.5mmol-73.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-108
 2-naphthaldehyde
(0.5mmol- 78.1mg)
 Methylamine
(0.5mmol-250uL)
 Quinic Acid
(0.5mmol-96.1mg)
 TOSMIC
(0.5mmol-97.6mg)
 Y No Ugi product
181-109
 3-methoxybenzaldehyde
(0.5mmol-61uL)
 1-hexylamine
(0.5mmol-66ul)
 4-hydroxybenzoic acid
(0.5mmol-69mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-110
 Salicylaldehyde
(0.5mmol-53.3uL)
 Aniline
(0.5mmol-45.5uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-111
 Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
 Methylamine
(0.5mmol-250uL)
 2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
 t-butylisocyanide
(0.5mmol-57.5uL)
 Reactants
Insoluble
181-112
 4-methoxybenzaldehyde
(0.5mmol-60.8uL)
 Methylamine
(0.5mmol-250uL)
 2,3-dihydroxybenzoic acid
(0.5mmol-77.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-113
 Veratraldehyde
(0.5mmol-83.1mg)
 3-Chloroaniline
(0.5mmol-53uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-114
 Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
 5-Methylfurfurylamine
(0.5mmol-55.7uL)
 2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
 n-butylisocyanide
(0.5mmol-53uL)
 Reactants
Insoluble
181-115
 2-naphthaldehyde
(0.5mmol- 78.1mg)
 3-Chloroaniline
(0.5mmol-53uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 t-butylisocyanide
(0.5mmol-57.5uL)
 Reactants
Insoluble
181-116
 4-chlorobenzaldehyde
(0.5mmol-70.3mg)
 Methylamine
(0.5mmol-250uL)
 2,3-dihydroxybenzoic acid
(0.5mmol-77.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-117
 Veratraldehyde
(0.5mmol-83.1mg)
 Furfurylamine
(0.5mmol-44.2uL)
 2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
 TOSMIC
(0.5mmol-97.6mg)
 Reactants
Insoluble
181-118
 5-bromo-2-thiophenecarboxaldehyde (0.5mmol-59.4uL)
 Methylamine
(0.5mmol-250uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 TOSMIC
(0.5mmol-97.6mg)
 N
181-119
 3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
 Methylamine
(0.5mmol-250uL)
 diphenylaceitc acid
(0.5mmol-106.1mg)
 n-butylisocyanide
(0.5mmol-53uL)
 N
181-120
 3,5-Bis(trifluoromethyl)benzaldehyde
(0.5mmol-121.0mg-??)
 Methylamine
(0.5mmol-250uL)
 2,4,6-trihydroxybenzoic acid.H2O
(0.5mmol-94mg)
 TOSMIC (0.5mmol-97.6mg)
 N
181-121
 3,4-dihydroxybenzaldehyde
(0.5mmol-69.06mgl)
 3-Chloroaniline
(0.5mmol-53uL)
 4-chlorophenylacetic acid
(0.5mmol-85.3mg)
 TOSMIC (0.5mmol-97.6mg)
 N
181-122
 Veratraldehyde
(0.5mmol-83.1mg)
 2-Chloroaniline
(0.5mmol-52.6uL)
 4-hydroxybenzoic acid
(0.5mmol-69mg)
 TOSMIC (0.5mmol-97.6mg)
 N
181-123
 Phenanthrene-9-carboxaldehyde
(0.5mmol-103.1mg)
 Furfurylamine
(0.5mmol-44.2uL)
 3,4-dihydroxyphenylaceticacid
(0.5mmol-84.0mg)
 TOSMIC (0.5mmol-97.6mg)
 N
181-124
 Salicylaldehyde
(0.5mmol-53.3uL)
 Benzylamine
(0.5mmol-54.6uL)
 3-(4-Methoxyphenyl)propionic acid (0.5mmol-90.1mg
 TOSMIC (0.5mmol-97.6mg)
 N

Results

Exp ID
 Day1
 Day-3
 Final
 Analytical data
181-55
 181-55day1.JPG
 181-55day3.JPG

181-56
 181-56day1.JPG
 181-56day3.JPG
Reactants
Insoluble
181-57
 181-57day1.JPG
 181-57day3.JPG

181-59
 181-59day1.JPG
 181-59day3.JPG

181-60
 181-60day1.JPG
 181-60day3.JPG

181-62
 181-62day1.JPG
 181-62day3.JPG

181-63
 181-63day1.JPG
 181-63day3.JPG

181-64
 181-64day1.JPG
 181-64day3.JPG

181-65
 181-65day1.JPG
 181-65day3.JPG

181-66
 181-66day1.JPG
 181-66day3.JPG

181-67
 181-67day1.JPG
 181-67day3.JPG

181-68
 181-68day1.JPG
 181-68day3.JPG

181-69
 181-69day1.JPG
 181-69day3.JPG
Reactants
Insoluble
181-70
 181-70day1.JPG
 181-70day3.JPG
Reactants
Insoluble
181-71
 181-71day1.JPG
Day 1
 181-71day3.JPG
Day 3
 181-71day12.JPG
Day 12
 Amount: 46mg
Yield:
M.P : 169-171C
IR
HNMR
CNMR
FAB-MS
181-72
 181-72day1.JPG
 181-72day3.JPG

181-73
 181-73day1.JPG
 181-73day3.JPG

181-74
 181-74day1.JPG
 181-74day3.JPG

181-75
 181-75day1.JPG
 181-75day3.JPG

181-76
 181-76day1.JPG
 181-76day3.JPG

181-77
 181-77day1.JPG
 181-77day3.JPG
Reactants
Insoluble
181-78
 181-78day1.JPG
 181-78day3.JPG
Reactants
Insoluble
181-79
 181-79day1.JPG
 181-79day3.JPG
Reactants
Insoluble
181-80
 181-80day1.JPG
 181-80day3.JPG
HNMR
CNMR
IR
FAB-MS
Crystal Structure
181-81
 181-81day1.JPG
 181-81day3.JPG
Reactants
Insoluble
181-82
 181-82day1.JPG
 181-82day3.JPG

181-83
 181-83day1.JPG
 181-83day3.JPG
Reactants
Insoluble
181-84
 181-84day1.JPG
 181-84day3.JPG

181-85
 181-85day1.JPG
 181-85day3.JPG

181-86
 181-86day1.JPG
 181-86day3.JPG

181-87
 181-87day1.JPG
 181-87day3.JPG
Reactants
Insoluble
181-88
 181-88day1.JPG
 181-88day3.JPG

181-89
 181-89day1.JPG
 181-89day3.JPG

181-90
 181-90day1.JPG
 181-90day3.JPG
Reactants
Insoluble
181-92
 181-92day1.JPG
 181-92day3.JPG

181-93
 181-93day1.JPG
 181-93day3.JPG

181-94
 181-94day1.JPG
 181-94day3.JPG

181-96
 181-96day1.JPG
 181-96day3.JPG

181-97
 181-97day1.JPG
 181-97day3.JPG

181-98
 181-98day1.JPG
 181-98day3.JPG

181-99
 181-99day1.JPG
 181-99day3.JPG

181-100
 181-100day1.JPG
 181-100day3.JPG
Reactants
Insoluble
181-101
 181-101day1.JPG
 181-101day3.JPG
Reactants
Insoluble
181-102
 181-102day1.JPG
 181-102day3.JPG

181-103
 181-103day1.JPG
 181-103day3.JPG

181-104
 181-104day1.JPG
 181-104day3.JPG

181-105
 181-105day1.JPG
 181-105day3.JPG

181-106
 181-106day1.JPG
 181-106day3.JPG

181-107
 181-107day1.JPG
 181-107day3.JPG

181-108
 181-108day1.JPG
Day 1
 181-108day3.JPG
Day 3
 181-108day12.JPG
Day 12
 Amount: 16mg -
Isoluble in DMSO-D6
Yield
M.P: 203-205C
IR
FAB-MS
181-109
 181-109day1.JPG
 181-109day3.JPG

181-110
 181-110day1.JPG
 181-110day3.JPG

181-111
 181-111day1.JPG
 181-111day3.JPG
Reactants
Insoluble
181-112
 181-112day1.JPG
 181-112day3.JPG

181-113
 181-113day1.JPG
 181-113day3.JPG

181-114
 181-114day1.JPG
 181-114day3.JPG
Reactants
Insoluble
181-115
 181-115day1.JPG
 181-115day3.JPG
Reactants
Insoluble
181-116
 181-116day1.JPG
 181-116day3.JPG

181-117
 181-117day1.JPG
 181-117day3.JPG
Reactants
Insoluble
181-118
 181-118day1.JPG
 181-118day1.JPG

181-119
 181-119day1.JPG
 181-119day1.JPG

181-120
 181-120day1.JPG
 181-120day1.JPG

181-121
 181-121day1.JPG
 181-121day1.JPG

181-122
 181-122day1.JPG
 181-122day1.JPG

181-123
 181-123day1.JPG
 181-123day1.JPG

181-124
 181-124day1.JPG
 181-124day1.JPG


Discussion

181-71 From the HNMR of the sample it is obvious that the solid obtained is not a clean ugi product, if at all. Similarly 181-108, the FAB MS shows no peaks corresponding to a ugi product. It is beyond the scope of this project to isolate or determine the nautre of these compounds.

Conclusions

No Ugi products isolated from this experiment.

Log

2008-04-09
13:00 Made up a solution of each aldehyde in methanol in vials labelled with Exp-Rank number. 2ml of methanol was used in vials which did not use methyl amine (in methanol solution). Vials which used methyl amine as the amine component used only 1850uL of methanol. Each vial was vortexed for 30s. Phenanthrene-9-Carboxaldehyde (181-55,56,75,79,103,111,114,123) and 4,7-dimethoxy-1-naphthaldehyde (181-101) did not go in solution.
Weights of dry,empty vials with labels and no cap-
181-055- 4.7012g
181-056- 4.6561g
181-057- 4.6500g
181-059- 4.6503g
181-060- 4.6620g
181-061- 4.6585g
181-062- 4.6755g
181-063- 4.7131g
181-064- 4.7336g
181-065- 4.6360g
181-066- 4.6888g
181-067- 4.6888g
181-068- 4.6744g
181-069- 4.6813g
181-070- 4.6575g
181-071- 4.6683g
181-072- 4.6789g
181-073- 4.6613g
181-074- 4.6420g
181-075- 4.6650g
181-076- 4.6905g
181-077- 4.6530g
181-078- 4.6733g
181-079- 4.6621g
181-080- 4.6685g
181-081- 4.6540g
181-082- 4.6532g
181-083- 4.6900g
181-084- 4.6943g
181-085- 4.6545g
181-086- 4.6466g
181-087- 4.6879g
181-088- 4.6700g
181-089- 4.6788g
181-090- 4.6638g
181-092- 4.6990g
181-093- 4.6676g
181-094- 4.6493g
181-096- 4.6820g
181-097- 4.6760g
181-098- 4.6610g
181-099- 4.6677g
181-100- 4.6600g
181-101- 4.6686g
181-102- 4.6785g
181-103- 4.6673g
181-104- 4.6729g
181-105- 4.6545g
181-106- 4.6545g
181-107- 4.6795g
181-108- 4.6786g
181-109- 4.6900g
181-110- 4.6700g
181-111- 4.6675g
181-112- 4.6415g
181-113- 4.6558g
181-114- 4.6785g
181-115- 4.6902g
181-116- 4.6684g
181-117- 4.6600g
181-118- 4.6712g
181-119- 4.6530g
181-120- 4.6618g
181-121- 4.6700g
181-122- 4.6655g
181-123- 4.6560g
181-124- 4.6948g
15:30 Added respective amines to each vial. Vortexed for 30s.
2008-04-10
23:00 Completed addition of respective acids to each vial. The vials were vortexed for 30s each after the acid addition.
2008-04-14
22:30 Completed addition of respective isocyanides to each vial. The vials were vortexed for 30s each after the isocyanide addition; obtained picture of the vials -(Day-1 series)
2008-04-16
16:50 Obtained pictures of the vials-(Day-3 series)
2008-04-23
11:45 Vortexed vial containing solutions 181-055 -181-124 for 15s each. Solution number 181-100 previously reported as 'reactants insoluble' has now turned clear.
2008-04-25
10:00 Observed solid in vials 181-71 and 181-108; obtained pictures.
2008-04-30
14:00 Vortexed 181-71 and 181-108 for 30s each, centrifuged them for 1min and decanted the supernatant. The residue was washed with methanol (3x 1000uL) each time vortexing the solution for 30s and centrifuging for 1min before decanting the supernatant.
15:45 The residues from 181-71 and 181-108 were set on high vac.
18:45 Removed them from high vac and obtained the now renamed 181-71A (46 mg) and 181-108A (16 mg)

Tags

Chemical
 Inchi
 Inchikey
benzaldehyde
 InChI=1/C7H6O/c8-6-7-4-2-1-3-5-7/h1-6H
 HUMNYLRZRPPJDN-UHFFFAOYAE
3-methoxybenzaldehyde
 InChI=1/C8H8O2/c1-10-8-4-2-3-7(5-8)6-9/h2-6H,1H3/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-16,10-16
 WMPDAIZRQDCGFH-UHFFFAOYAC
Phenanthrene-9-carboxaldehyde
 InChI=1/C15H10O/c16-10-12-9-11-5-1-2-6-13(11)15-8-4-3-7-14(12)15/h1-10H
 QECIGCMPORCORE-UHFFFAOYAE
Salicylaldehyde
 InChI=1/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H
 SMQUZDBALVYZAC-UHFFFAOYAD
3,4-dimethoxybenzaldehyde
 InChI=1/C9H10O3/c1-11-8-4-3-7(6-10)5-9(8)12-2/h3-6H,1-2H3
 WJUFSDZVCOTFON-UHFFFAOYAT
4-methylbenzaldehyde
 InChI=1/C8H8O/c1-7-2-4-8(6-9)5-3-7/h2-6H,1H3/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-16
2-naphthaldehyde
 InChI=1/C11H8O/c12-8-9-5-6-10-3-1-2-4-11(10)7-9/h1-8H
 PJKVFARRVXDXAD-UHFFFAOYAM
2,3-dihydroxybenzaldehyde
 InChI=1/C7H6O3/c8-4-5-2-1-3-6(9)7(5)10/h1-4,9-10H
 IXWOUPGDGMCKGT-UHFFFAOYAD
4-chlorobenzaldehyde
 InChI=1/C7H5ClO/c8-7-3-1-6(5-9)2-4-7/h1-5H
 AVPYQKSLYISFPO-UHFFFAOYAQ
4-methoxybenzaldehyde
 InChI=1/C8H8O2/c1-10-8-4-2-7(6-9)3-5-8/h2-6H,1H3
 ZRSNZINYAWTAHE-UHFFFAOYAA
3,4-dihydroxybenzaldehyde
 nChI=1/C7H6O3/c8-4-5-1-2-6(9)7(10)3-5/h1-4,9-10H
 IBGBGRVKPALMCQ-UHFFFAOYAN
3-hydoxybenzaldehyde
 InChI=1/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H
 IAVREABSGIHHMO-UHFFFAOYAC
3,5-dimethoxybenzaldehyde
 InChI=1/C9H10O3/c1-11-8-3-7(6-10)4-9(5-8)12-2/h3-6H,1-2H3
 VFZRZRDOXPRTSC-UHFFFAOYAG
4,7-Dimethoxy-1-naphthaldehyde
 InChI=1/C13H12O3/c1-15-10-4-5-11-12(7-10)9(8-14)3-6-13(11)16-2/h3-8H,1-2H3
 FFAODEUKHYBIKI-UHFFFAOYAI
5-methylfurfurylamine
 InChI=1/C6H9NO/c1-5-2-3-6(4-7)8-5/h2-3H,4,7H2,1H3
 YSEAGSCGERFGBL-UHFFFAOYAH
furfurylamine
 InChI=1/C5H7NO/c6-4-5-2-1-3-fu7-5/h1-3H,4,6H2c
 DDRPCXLAQZKBJP-UHFFFAOYAX
methylamine
 InChI=1/CH5N/c1-2/h2H2,1H3
 BAVYZALUXZFZLV-UHFFFAOYAN
n-propylamine
 InChI=1/C3H9N/c1-2-3-4/h2-4H2,1H3
 WGYKZJWCGVVSQN-UHFFFAOYAG
aniline
 InChI=1/C6H7N/c7-6-4-2-1-3-5-6/h1-5H,7H2
 PAYRUJLWNCNPSJ-UHFFFAOYAP
3-chloroaniline
 InChI=1/C6H6ClN/c7-5-2-1-3-6(8)4-5/h1-4H,8H2/i1-12,2-12,3-12,4-12,5-12,6-12,7-35,8-14
3,4-dihydroxyphenylacetiacid
 InChI=1/C8H8O4/c9-6-2-1-5(3-7(6)10)4-8(11)12/h1-3,9-10H,4H2,(H,11,12)
 CFFZDZCDUFSOFZ-UHFFFAOYAU
5-nitrosalicylic acid
 InChI=1/C7H5NO5/c9-6-2-1-4(8(12)13)3-5(6)7(10)11/h1-3,9H,(H,10,11)
 PPDRLQLKHRZIJC-UHFFFAOYAT
benzoic acid
 InChI=1/C7H6O2/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H,8,9)
 WPYMKLBDIGXBTP-UHFFFAOYAD
Boc-L-tryptophan
 InChI=1/C1 ​6H20N2O4/c​1-16(2,3)2​2-15(21)18​-13(14(19)​20)8-10-9-​17-12-7-5-​ 4-6-11(10)​12/h4-7,9,​13,17H,8H2​,1-3H3,(H,​18,21)(H,1​9,20)
 NFVNYBJCJGKVQK-UHFFFAOYAR
2,4,6-trihydroxybenzoicacid
 InChI=1/C7H6O5/c8-3-1-4(9)6(7(11)12)5(10)2-3/h1-2,8-10H,(H,11,12)
 IBHWREHFNDMRPR-UHFFFAOYAP
2-methylpropeneoicacid
 InChI=1/C4H6O2/c1-3(2)4(5)6/h1H2,2H3,(H,5,6)
 CERQOIWHTDAKMF-UHFFFAOYAE
(±)-2-Phenylbutanoic acid
 InChI=1/C10H12O2/c1-2-9(10(11)12)8-6-4-3-5-7-8/h3-7,9H,2H2,1H3,(H,11,12)
 OFJWFSNDPCAWDK-UHFFFAOYAE
D-(−)-Quinic acid
 InChI=1/C7H12O6/c8-3-1-7(13,6(11)12)2-4(9)5(3)10/h3-5,8-10,13H,1-2H2,(H,11,12)/t3-,4-,5?,7?/m1/s1
 AAWZDTNXLSGCEK-LNVDRNJUBH
n-butanoic acid
 InChI=1/C4H8O2/c1-2-3-4(5)6/h2-3H2,1H3,(H,5,6)
 FERIUCNNQQJTOY-UHFFFAOYAP
Mandelic acid
 InChI=1/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1
 IWYDHOAUDWTVEP-ZETCQYMHBP
2-Hydroxy-5-nitrobenzoicacid
 InChI=1/C7H5NO5/c9-6-2-1-4(8(12)13)3-5(6)7(10)11/h1-3,9H,(H,10,11)
 PPDRLQLKHRZIJC-UHFFFAOYAT
(2,5-Dimethoxyphenyl)acetic acid
 InChI=1/C10H12O4/c1-13-8-3-4-9(14-2)7(5-8)6-10(11)12/h3-5H,6H2,1-2H3,(H,11,12)
 BBZDYQUXRFATHZ-UHFFFAOYAX
TOSMIC
 InChI=1/C9H9NO2S/c1-8-3-5-9(6-4-8)13(11,12)7-10-2/h3-6H,7H2,1H3
 CFOAUYCPAUGDFF-UHFFFAOYA
n-butylisocyanide
 InChI=1/C5H9N/c1-3-4-5-6-2/h3-5H2,1H3
 FSBLVBBRXSCOKU-UHFFFAOYAR
t-butylisocyanide
 InChI=1/C5H9N/c1-5(2,3)6-4/h1-3H3
 FAGLEPBREOXSAC-UHFFFAOYAL
4-hydroxybenzoic acid
 InChI=1/C7H6O3/c8-6-3-1-5(2-4-6)7(9)10/h1-4,8H,(H,9,10)
 FJKROLUGYXJWQN-UHFFFAOYAQ
2,5-dimethoxyphenylacetic acid
 InChI=1/C10H12O4/c1-13-8-3-4-9(14-2)7(5-8)6-10(11)12/h3-5H,6H2,1-2H3,(H,11,12)
 BBZDYQUXRFATHZ-UHFFFAOYAX
diphenylacetic acid
 InChI=1/C14H12O2/c15-14(16)13(11-7-3-1-4-8-11)12-9-5-2-6-10-12/h1-10,13H,(H,15,16)
 PYHXGXCGESYPCW-UHFFFAOYAC
3-methylbut-2-enoic acid
 InChI=1/C5H8O2/c1-4(2)3-5(6)7/h3H,1-2H3,(H,6,7)
 YYPNJNDODFVZLE-UHFFFAOYAX
2,6-dihydroxybenzoic aicd
 InChI=1/C7H6O4/c8-4-2-1-3-5(9)6(4)7(10)11/h1-3,8-9H,(H,10,11)
 AKEUNCKRJATALU-UHFFFAOYAG
Phenylpropynoic acid
 InChI=1/C9H6O2/c10-9(11)7-6-8-4-2-1-3-5-8/h1-5H,(H,10,11)
 XNERWVPQCYSMLC-UHFFFAOYAX
1-hexylamine
 InChI=1/C6H15N/c1-2-3-4-5-6-7/h2-7H2,1H3
 BMVXCPBXGZKUPN-UHFFFAOYAQ
Benzylamine
 InChI=1/C7H9N/c8-6-7-4-2-1-3-5-7/h1-5H,6,8H2
 WGQKYBSKWIADBV-UHFFFAOYAL
3-hydroxybenzaldehyde
 InChI=1/C7H6O2/c8-5-6-2-1-3-7(9)4-6/h1-5,9H
 IAVREABSGIHHMO-UHFFFAOYAC
2,4,6-trimethylbenzaldehyde
 InChI=1/C10H12O/c1-7-4-8(2)10(6-11)9(3)5-7/h4-6H,1-3H3/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-12,1-12,11-16
2-methylbenzaldehyde
 InChI=1/C8H8O/c1-7-4-2-3-5-8(7)6-9/h2-6H,1H3/i1-12,2-12,3-12,4-12,5-12,6-12,7-12,8-12,9-16
2-Hydroxybenzaldehyde
InChI=1/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H
 SMQUZDBALVYZAC-UHFFFAOYAD